Gossip Girl: The Awkward Years
by FireCube
Summary: In the show, everyone look handsome and beautiful, but what happens if we dial it back a few years? Middle school, puberty, the whole shebang. Witness it all here!


The light bree ze ruffled the red and orange leaves that signaled the beginning of fall. On the Upper East Side, fall means school; and with school entails countless trips to the mall, choosing enough outfits to clothe a poor family for an entire year. School for these prestigious younglings is merely a place to exhibit their wealth, and reign supreme over the other less wealthy and powerful children.

 _Hello Upper East Siders, Gossip Girl here, your one and only source into the scandalous lives of Manhattan's elite. I hear a new season and a new school year are around the corner; fall and middle school. Who will we see fall from the tree of the select few Upper East Siders and who will rise to the occasion? Happy Falling! XOXO_

 _-Gossip Girl_

 **September 19** **th** **, 2004 Serena**

Serena van der Woodsen clacked around her spacious apartment in her 5-inch heels in search of the perfect pair of earrings to wear for the first day of sixth grade. Due to her tall stature, Serena didn't need heels; she was already taller than most of the guys in her grade. The only reason Serena wore heels was to feel powerful and significant, just like her mother, Lily van der Woodsen, who ruled the socialites of the Upper East Side.

"It sounds like there is a typewriter is being smashed in here, what on earth can you possibly be doing running around at 7:30 in the morning?" Lily asked groggily as she rubbed her eyes.

"Looking for my earrings," Serena replied, rolling her eyes. Lily sighed as she scanned the apartment for suitable earrings for her daughter to wear to school.

"What about these over here?" Lily asked as she pulled a pair of silver earrings off of her table and handed them to Serena.

"Nope," Serena replied with no hesitation. "Too shiny. I want to wear emerald earrings, to match my dress," she said as she twirled around to show her mother the beautiful Louis Vuitton dress she had picked out. Serena felt like she could take on the world. She knew that middle school was the first place where she could really stand out among the crowd, and she planned to do so in style.

Lily sighed as she opened a drawer in her desk. She pulled out a gorgeous pair of circular emerald earrings that seemed to glow, although that may have just been the way the sun reflected off of them. Serena let out a gasp when she saw them and ran over to her mother, creating another cacophony of footsteps. Grabbing the delicate earrings out of her mothers' hand, Serena hurriedly put them on.

"They look amazing!" Serena exclaimed after eyeing herself in a mirror. She ran to the elevator to go to school when she realized she had forgotten her backpack. She sighed and made the treacherous journey back to her room to grab one of many Gucci handbags and filled it to the brim with her phone, her makeup, her laptop, and a few books and pens scattered here and there.

After exiting the elevator and entering the lobby, she spotted several paparazzi eagerly waiting outside, all hoping to get the best picture of Manhattan's potentially new "it" girl. Serena straightened her back and put on a smile that would have melted a rock. She opened the door to exit the lobby and posed, allowing more pictures to be taken. After several hundred flashes had gone off, she entered the waiting limo and set off for school.

 **Dan**

BEEP! BEEP! BEEP!

Dan turned over in bed and smashed the snooze button out of habit. Rubbing his eyes, he pulled off the covers and tried to focus on the clock. As his eyes slowly focused, he made out the numbers 7:30. Sighing heavily, he fell back into bed and tried to fall back asleep.

Having attended public school up until fifth grade, Dan was not at all excited for his first day at Constance Middle School. All he expected were snotty rich kids whose worst problems included not getting enough allowance and having too many clothes to choose from.

"DAN, GET THE HELL OUT OF BED, YOU'LL BE LATE FOR SCHOOL!" Rufus shouted.

Dan let out a snort as he thought of his over-protective father. Even though Rufus cared immensely for him, Dan felt Rufus was intrusive at times.

After his daily morning routine, Dan walked into the kitchen and sat down in a chair.

"Nice of you to join us," Rufus said sarcastically, opening the morning paper. He poured himself a glass of orange juice and brought out two bowls for his two children, Dan and Jenny.

"Nice of you to wake me up," Dan retorted playfully. As he poured out some cereal, Jenny walking into the kitchen, wearing what seemed like ten pounds of make-up. Unlike Dan, Jenny had been at Constance Elementary since the first grade. She had already learnt the way of the upper east siders, all dolled up in make-up that made her seem ten years older. Jenny was getting ready for her first day of fourth grade.

"Hello daddy! Lovely day to start fourth grade, isn't it? It's not too hot or cold, so my hair won't frizz and I won't freeze to death," Jenny exclaimed, grabbing a cup of orange juice. Rufus offered her a bagel, but she refused, muttering something about "watching her figure before school starts". Rufus and Dan just thought that whole "diet" thing was just a myth, and acted as a gateway for young girls into anorexia. Rufus sighed as he realized arguing with his daughter would just be carrying coals to Newcastle. He had tried once before to make her eat a small sandwich, but she always vehemently refused. Those private school girls and their anorexic ways. Rufus just always resorted to adding higher-calories content foods to Jenny's lunches in an attempt to combat her refusal to consume a lot of food.

As Dan finished his bowl of cereal and Jenny finished her meager glass of orange juice, Rufus grabbed both of their backpacks, eyeing the clock.

"Come on! If you both don't move faster than a snail on a slow day, you'll be late for school!" This time, Dan and Jenny sighed together, amused at their father's odd sense of humor. They both put their eating devices in the sink as they grabbed their backpacks from their father.

"Have a lovely first day!" Rufus exclaimed as both children left. The door closed shut so Dan and Jenny didn't hear Rufus say "and good luck to you both".

A/N: It's like five in the morning and I found this story I apparently wrote, but don't even remember. Anyway, I added a couple hundred words and decided to upload for the heck of it. Happy reading! (I haven't watched gg in a while, so forgive any mishaps in that regard)


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